35 days in Chicago Itinerary

35 days in Chicago Itinerary

Created using Inspirock Chicago holiday maker

Make it your trip
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Chicago
— 34 nights

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Chicago

— 34 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get out of town with these interesting Chicago side-trips: Rotary Botanical Gardens (in Janesville), Prairie States Winery (in Genoa) and DC Estate Winery (in South Beloit). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, brush up on your knowledge of spirits at Whiskey Acres Distilling Co., try your luck at Horseshoe Hammond, and stroll through Millennium Park.

For traveler tips, maps, reviews, and other tourist information, read Chicago sightseeing planner.

Expect a daytime high around 38°F in December, and nighttime lows around 26°F.

Things to do in Chicago

Historic Sites · Parks · Museums · Neighborhoods

Side Trips